“There’s a barbecue and a bar area. And the idea is that most of the people who build companies at TechNexus, these are startups. These are entrepreneurs,” he said. “We’re here 12, 15, 18 hours a day, and in some cases 24 hours a day and sleeping on the floor of the office,” he said.

Deciding where the bar should go on a new company’s rooftop deck isn’t a decision most would’ve thought Howerton would be making at this point in his career. A few years ago, another high profile business of his took a nose dive.

But in Howerton’s words, starting new businesses is simply part of his DNA -- even when they sometimes fail. He’s always considered himself an entrepreneur, as far back as the second grade.

“I realized the pencil machine outside of the principal’s office that sold pencils two for a quarter, you could buy all the pencils out of the machine. It took the principal two weeks to restock the machine,” he said. “So if you cornered the market on pencils, you could sell them for a quarter apiece.”

Howerton said he must’ve started 20 to 30 companies over his lifetime. He dropped out of college his freshman year because he wanted to work on a business idea, instead of sitting bored in class.

In 2001, he moved to Chicago to launch a tech firm called Fast Root. It was a company that delivered software on the Internet. Things were going well for the business. So Howerton started launching other projects, like a tech incubator that would later become TechNexus.

But after awhile he found himself losing zeal for FastRoot. And maybe that was the tip of the iceberg.

“We were very ambitious at FastRoot, and had planned on building several new data centers, had projects underway, very expensive projects we were spending money on,” he recalled. “When the market shifted in 2008, because I wasn’t really focused completely on the business, I think we weren’t agile enough to respond.”

One of the other ventures he was juggling back then was a charter school that he helped build. It taught inner city kids about entrepreneurship and technology. Howerton said as FastRoot starting tanking, he found himself telling the students that failure was part of entrepreneurship. But here he was unable to accept it.

“I think there’s a thin line between entrepreneurs who think people telling them something is impossible is completely plausible,” he said. “The idea that I’m going to fight that battle until I win that battle, which is something that’s just ingrained in an entrepreneur. And the idea of being able to accept failure fast enough.”

For something that could’ve been over in 60 days, the FastRoot failure dragged out painfully for a year and a half. Howerton said he began doubting himself and had no energy to create new things.

“I think a part of that time, as the Titanic was sinking, as the business was failing, and a part of that time was licking my wounds after that failure. And that’s what failure does to an entrepreneur. It really distracts them from other opportunities for success,” he said.

And then Howerton faced a kind of crossroads. He was offered a job at another company, a good position with a nice salary. He turned it down.

“What finally helped me break out of the cycle was to realize that that wasn’t me. It had never been me in 25 years of being an entrepreneur, and I didn’t want it to be me for the next 25 years,” he said.

Howerton doesn't remember this period fondly.

“It was pretty visible, and lots of gossips and gadflies and bloggers like to write about it and poke fun about it, but it’s made me stronger,” he said.

Strong enough even to face his old failures. After he finishes the TechNexus build out, Howerton said he plans to give FastRoot another try.

“At What Cost?” is made possible in part by the John A. Wing Society, an initiative of the Illinois Humanities Council to improve dialogue about business and the common good.